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Cabo San Lucas

$103+ Cheap flights from Chicago (CHI) to Cabo San Lucas, Mexico

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Cabo San Lucas are usually found in July or August, booked 49 days in advance, depart on a Tuesday or Monday and return on a Saturday

Cheap flight deals from Chicago to Cabo San Lucas

Keep the following information in mind while searching for Chicago to Cabo San Lucas flight deals. Data was last updated April 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$378
(Trip.com)

One-way from

$103
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$554
Provider with most accurate pricing for Chicago (CHI)-San José del Cabo Los Cabos flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-San José del Cabo Los Cabos flights.
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From Chicago (CHI) to Cabo San Lucas
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One-way flight from Chicago (CHI) to Cabo San Lucas
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Highest demand for flights based on searches. 6% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Chicago to Cabo San Lucas

Cheapest flights from Chicago to Cabo San Lucas
Explore the most affordable flight options available from Chicago to Cabo San Lucas. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 3, 2025.

This Trip.com deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/161:45 amORD - SJD
1 stop8h 02mVolaris
Sat 5/243:32 pmSJD - ORD
1 stop6h 43mVolaris
Deal found 4/2$378
This Kiwi.com deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/161:45 amORD - SJD
1 stop15h 05mMultiple Airlines
Sat 5/249:15 amSJD - ORD
2 stops12h 20mMultiple Airlines
Deal found 4/2$379
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/262:40 pmMDW - SJD
2 stops19h 20mMultiple Airlines
Sat 5/38:22 amSJD - MDW
1 stop8h 44mMultiple Airlines
Deal found 4/1$380
This Kiwi.com deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/212:35 pmORD - SJD
1 stop10h 00mViva
Wed 6/119:00 amSJD - ORD
2 stops12h 45mViva
Deal found 4/2$383
This American Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/115:00 amORD - SJD
1 stop9h 25mAmerican Airlines
Wed 5/1412:50 pmSJD - ORD
Nonstop4h 20mAmerican Airlines
Deal found 4/2$433
This Alaska Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/37:13 pmORD - SJD
1 stop19h 16mAlaska Airlines
Fri 5/93:34 pmSJD - ORD
1 stop12h 31mAlaska Airlines
Deal found 4/2$444
This Mytrip deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/128:39 pmMDW - SJD
1 stop13h 08mVolaris
Fri 5/1612:01 pmSJD - MDW
1 stop29h 05mVolaris
Deal found 4/2$448
This Hawaiian Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/37:13 pmORD - SJD
1 stop19h 16mHawaiian Airlines
Sat 5/104:45 pmSJD - ORD
1 stop23h 35mHawaiian Airlines
Deal found 4/2$470
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2911:07 amORD - SJD
2 stops12h 42mDelta
Mon 6/912:53 pmSJD - ORD
1 stop9h 00mDelta
Deal found 4/2$476
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/176:00 amMDW - SJD
2 stops14h 15mDelta
Sat 5/246:06 amSJD - MDW
2 stops13h 07mDelta
Deal found 4/2$486
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/135:30 amMDW - SJD
2 stops8h 40mSouthwest
Fri 5/1612:30 pmSJD - MDW
1 stop9h 35mSouthwest
Deal found 4/2$503
This United Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/258:45 amORD - SJD
Nonstop4h 43mUnited Airlines
Mon 5/52:50 pmSJD - ORD
1 stop16h 43mUnited Airlines
Deal found 4/2$507

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Cabo San Lucas that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 3, 2025.
Use the filters below to find and compare flights from Chicago to Cabo San Lucas that are best for you.

Fly from

Chicago

Fly to

Cabo San Lucas

Route

Depart

Return

Price

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 5/16

1:45 am-7:47 am

1 stop8h 02m

San José del Cabo Los Cabos

Sat 5/24

3:32 pm-12:15 am

1 stop6h 43m

$378

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 5/16

1:45 am-2:50 pm

1 stop15h 05m

San José del Cabo Los Cabos

Sat 5/24

9:15 am-11:35 pm

2 stops12h 20m

$379

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 4/26

2:40 pm-8:00 am

2 stops19h 20m

San José del Cabo Los Cabos

Sat 5/3

8:22 am-7:06 pm

1 stop8h 44m

$380

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 6/2

12:35 pm-8:35 pm

1 stop10h 00m

San José del Cabo Los Cabos

Wed 6/11

9:00 am-11:45 pm

2 stops12h 45m

$383

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sun 5/11

5:00 am-12:25 pm

1 stop9h 25m

San José del Cabo Los Cabos

Wed 5/14

12:50 pm-7:10 pm

Nonstop4h 20m

$433

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 5/3

7:13 pm-12:29 pm

1 stop19h 16m

San José del Cabo Los Cabos

Fri 5/9

3:34 pm-6:05 am

1 stop12h 31m

$444

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 5/12

8:39 pm-7:47 am

1 stop13h 08m

San José del Cabo Los Cabos

Fri 5/16

12:01 pm-7:06 pm

1 stop29h 05m

$448

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 5/3

7:13 pm-12:29 pm

1 stop19h 16m

San José del Cabo Los Cabos

Sat 5/10

4:45 pm-6:20 pm

1 stop23h 35m

$470

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 5/29

11:07 am-9:49 pm

2 stops12h 42m

San José del Cabo Los Cabos

Mon 6/9

12:53 pm-11:53 pm

1 stop9h 00m

$476

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 5/17

5:30 am-10:40 am

1 stop7h 10m

San José del Cabo Los Cabos

Wed 5/21

11:40 am-8:15 pm

1 stop6h 35m

$486

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 27 results
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Best time to book a flight from Chicago to Cabo San Lucas

Have a flexible travel schedule? Discover the best time to fly to Cabo San Lucas from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Cabo San Lucas

How far ahead should I book a flight from Chicago to Cabo San Lucas?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Cabo San Lucas. Price data was last updated on March 28, 2025.

Booking 49 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Cabo San Lucas. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Cabo San Lucas?

Currently, January is the cheapest month in which you can book a flight from Chicago to Cabo San Lucas (average of $437). Flying from Chicago to Cabo San Lucas in June is currently the most expensive (average of $560). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to C4B?

Find hourly flight availability from Chicago to Cabo San Lucas. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 3, 2025.

When flying from Chicago to Cabo San Lucas, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Cabo San Lucas

Explore weekly flight availability from Chicago to Cabo San Lucas. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 3, 2025.

The most flights from CHI to C4B are scheduled on a Monday (4 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Cabo San Lucas by month

Plan your trip to Cabo San Lucas by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Cabo San Lucas ranges from 0.0 - 4.5 inches per month. September is typically the wettest month, when rainfall can reach 4.5 in. March is typically the driest time to visit Cabo San Lucas when rainfall is around 0.0 in.

Temperature in Cabo San Lucas by month

Plan your trip to Cabo San Lucas by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Cabo San Lucas, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 66.2 F).

Reviews of airlines servicing Cabo San Lucas

Get insights into the airlines that provide service to Cabo San Lucas. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cabo San Lucas. Reviews last updated April 3, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Chicago to Cabo San Lucas by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,831 reviews

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,831 reviews
Alaska Airlines
8.0
Very good
9,831 reviews

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,274 reviews
Alaska Airlines
8.0
Very good
9,831 reviews

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,897 reviews
Alaska Airlines
8.0
Very good
9,831 reviews

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Hawaiian Airlines
7.9
Good
2,344 reviews
Alaska Airlines
8.0
Very good
9,831 reviews

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Aeromexico
7.5
Good
1,700 reviews
Alaska Airlines
8.0
Very good
9,831 reviews

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

Find useful and relevant information for your journey from Chicago to Cabo San Lucas. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Cabo San Lucas one-way?

    One-way options have recently been found by users for as low as $122 on Volaris. Other airlines that offer cheap prices include Viva from $142 and Delta from $179 one-way.

  • What are the most reliable airlines from Chicago to Cabo San Lucas?

    The top 3 most reliable airlines when flying from Chicago to Cabo San Lucas are Emirates (89%), American Airlines (87%) and United Airlines (69%).

  • What are the cheapest flights from Chicago to Cabo San Lucas?

    While on average a flight from Chicago to Cabo San Lucas is generally $512, our data shows the cheapest flight currently is $245. When looking at the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos), you can expect to pay $290 for that flight.

  • Can I find deals for flights from Chicago to Cabo San Lucas that include hotel bookings?

    Yes. In addition to deals on Chicago to Cabo San Lucas flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Cabo San Lucas?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Cabo San Lucas.

  • Can I find deals for business class flights from Chicago to Cabo San Lucas?

    Yes. Cheapflights offers flight deals from Chicago to Cabo San Lucas by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Cabo San Lucas?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Cabo San Lucas (average of $437). Flying from Chicago to Cabo San Lucas in June is currently the most expensive (average of $560). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 7 airlines flying from Chicago to Cabo San Lucas

Discover the top 7 airlines that operate flights from Chicago to Cabo San Lucas. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$268Average$382FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$287Average$417FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$426Average$590FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$437Average$634FlexibilityNo cancel feeOn-time71%
DeltaCheapest$445Average$607FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$451Average$684FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$545Average$720FlexibilityNo cancel feeOn-time63%

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